WO2010061182A3 - Process for preparing zanamivir and intermediates for use in the process - Google Patents

Process for preparing zanamivir and intermediates for use in the process Download PDF

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Publication number
WO2010061182A3
WO2010061182A3 PCT/GB2009/002744 GB2009002744W WO2010061182A3 WO 2010061182 A3 WO2010061182 A3 WO 2010061182A3 GB 2009002744 W GB2009002744 W GB 2009002744W WO 2010061182 A3 WO2010061182 A3 WO 2010061182A3
Authority
WO
WIPO (PCT)
Prior art keywords
zanamivir
present
provides
preparing
triacetoxypropyl
Prior art date
Application number
PCT/GB2009/002744
Other languages
French (fr)
Other versions
WO2010061182A2 (en
Inventor
Manjinder Singh Phull
Rajendra Narayanrao Kankan
Dharmaraj Ramachandra Rao
Ashwini Amol Sawant
Sanoj Thoppil
Original Assignee
Cipla Limited
Curtis, Philip, Anthony
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cipla Limited, Curtis, Philip, Anthony filed Critical Cipla Limited
Priority to CA2744793A priority Critical patent/CA2744793A1/en
Priority to AU2009321347A priority patent/AU2009321347A1/en
Priority to EP09756775.4A priority patent/EP2358695B1/en
Priority to US13/130,692 priority patent/US8993789B2/en
Priority to ES09756775.4T priority patent/ES2507492T3/en
Priority to JP2011538048A priority patent/JP2012510456A/en
Publication of WO2010061182A2 publication Critical patent/WO2010061182A2/en
Publication of WO2010061182A3 publication Critical patent/WO2010061182A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring

Abstract

The present invention provides a process for preparing methyl 5-acetamido-4-amino-6- (1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (V), which process comprises reducing methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2- carboxylate (IV) in the presence of a reducing agent selected from the group consisting of lithium aluminium hydride, sodium borohydride, zinc/ammonium chloride, zinc-ferric chloride and ferric chloride/sodium iodide. The present invention also provides compounds of formula (VIII) and (IX) which may be used in the synthesis of zanamivir. The present invention also provides processes for preparing compounds (VIII) and (IX) and processes involving their use, including in the synthesis of zanamivir.
PCT/GB2009/002744 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process WO2010061182A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA2744793A CA2744793A1 (en) 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process
AU2009321347A AU2009321347A1 (en) 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process
EP09756775.4A EP2358695B1 (en) 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process
US13/130,692 US8993789B2 (en) 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process
ES09756775.4T ES2507492T3 (en) 2008-11-28 2009-11-24 Process to prepare zanamivir and intermediates for use in the process
JP2011538048A JP2012510456A (en) 2008-11-28 2009-11-24 Process for producing zanamivir and intermediate for use in the process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2502MU2008 2008-11-28
IN2502/MUM/2008 2008-11-28

Publications (2)

Publication Number Publication Date
WO2010061182A2 WO2010061182A2 (en) 2010-06-03
WO2010061182A3 true WO2010061182A3 (en) 2010-07-22

Family

ID=41693037

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2009/002744 WO2010061182A2 (en) 2008-11-28 2009-11-24 Process for preparing zanamivir and intermediates for use in the process

Country Status (9)

Country Link
US (1) US8993789B2 (en)
EP (2) EP2476675A1 (en)
JP (1) JP2012510456A (en)
KR (1) KR20110098760A (en)
AU (1) AU2009321347A1 (en)
CA (1) CA2744793A1 (en)
ES (1) ES2507492T3 (en)
WO (1) WO2010061182A2 (en)
ZA (1) ZA201104635B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111116533B (en) * 2013-09-09 2022-11-22 中国科学院上海有机化学研究所 Zanamivir and ranamivir intermediate and synthesis method thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8993789B2 (en) 2008-11-28 2015-03-31 Cipla Limited Process for preparing zanamivir and intermediates for use in the process
CN101962375B (en) * 2010-09-21 2012-05-23 仙居县圃瑞药业有限公司 Zanamivir intermediate azide reduction technical method
EP2678324A1 (en) * 2011-02-24 2014-01-01 Cadila Healthcare Limited Process for the preparation of zanamivir
GB201106095D0 (en) 2011-04-11 2011-05-25 Glycom As N-Substituted mannosamine derivatives, process for their preparation and use thereof
DE102011117128A1 (en) * 2011-10-28 2013-05-02 Christian-Albrechts-Universität Zu Kiel Compounds for the treatment of influenza

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823428A2 (en) * 1996-07-22 1998-02-11 Sankyo Company Limited Neuraminic acid derivatives, their preparation and their medical use

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SK282950B6 (en) 1990-04-24 2003-01-09 Biota Scientific Management Pty Ltd Alpha-D-neuraminic acid derivatives, their preparation method, use and pharmaceutical preparations based on them
AU659501B2 (en) 1991-10-23 1995-05-18 Biota Scientific Management Pty Ltd Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of alpha-D-neuraminic acid
GB9126725D0 (en) 1991-12-17 1992-02-12 Glaxo Group Ltd Process
GB9220327D0 (en) 1992-09-25 1992-11-11 Glaxo Group Ltd Process
GB9220241D0 (en) 1992-09-25 1992-11-11 Glaxo Group Ltd Process
US8993789B2 (en) 2008-11-28 2015-03-31 Cipla Limited Process for preparing zanamivir and intermediates for use in the process

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823428A2 (en) * 1996-07-22 1998-02-11 Sankyo Company Limited Neuraminic acid derivatives, their preparation and their medical use

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DOUGLAS S. JOHNSON AND JIE JACK LI: "The Art of Drug Synthesis", 6 July 2007, JOHN WILEY AND SONS, XP002571327 *
SMITH P ET AL: "Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, EDITIONS SCIENTIFIQUE ELSEVIER, PARIS, FR, vol. 31, no. 2, 1 January 1996 (1996-01-01), pages 143 - 150, XP004040101, ISSN: 0223-5234 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111116533B (en) * 2013-09-09 2022-11-22 中国科学院上海有机化学研究所 Zanamivir and ranamivir intermediate and synthesis method thereof

Also Published As

Publication number Publication date
EP2358695A2 (en) 2011-08-24
EP2476675A1 (en) 2012-07-18
US8993789B2 (en) 2015-03-31
ES2507492T3 (en) 2014-10-15
EP2358695B1 (en) 2014-07-02
ZA201104635B (en) 2012-10-31
CA2744793A1 (en) 2010-06-03
JP2012510456A (en) 2012-05-10
KR20110098760A (en) 2011-09-01
AU2009321347A1 (en) 2010-06-03
US20110257418A1 (en) 2011-10-20
WO2010061182A2 (en) 2010-06-03

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